Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.
J Org Chem. 2012 Aug 3;77(15):6394-408. doi: 10.1021/jo301288w. Epub 2012 Jul 24.
A new, highly efficient, and atom-economic access to a series of functionalized 2,5-disubstituted oxazoles from propargylic amides is reported. A series of propargylic amides were transformed to the corresponding alkylideneoxazolines by a gold(I) catalyst. The next step was an autoxidation to hydroperoxides bearing the heteroaromatic oxazoles. Experiments addressing the reaction mechanism reveal a radical pathway for this autoxidation process. The hydroperoxides could conveniently be converted to the corresponding alcohols by reduction with sodium borohydride.
本文报道了一种从丙炔酰胺合成一系列功能化 2,5-二取代恶唑的高效、原子经济性方法。一系列丙炔酰胺在金（I）催化剂的作用下转化为相应的亚烷基恶唑啉。下一步是通过自动氧化将杂芳基恶唑的过氧化物转化为过氧化物。对反应机理的实验研究揭示了该自动氧化过程的自由基途径。过氧化物可以通过用硼氢化钠还原方便地转化为相应的醇。
